From elephant hunter to bejeweled exhibitionist, the tortured
life of Gregory Hemingway.

By Nara Schoenberg CHICAGO TRIBUNE

November 19, 2001

Miami

ON HIS last night as a free man, Ernest Hemingway's youngest
son slipped on a demure black cocktail dress and made his way
to a small private party in the upscale Miami enclave of Coconut
Grove.

He introduced himself to friends as "Vanessa" and
spent much of the evening in the kitchen, chatting with millionaires
in country club attire. Guests say he didn't get drunk. He seemed
to be in good spirits.

"The odd thing about it was, he looked happy," says
writer Peter Myers, who had never seen his old friend dressed
as a woman before.

"I'd say he looked about 20 years younger. He looked comfortable."
But things took a rapid turn for the worse, as things often did
in the life of Gregory Hemingway, a doctor who had lost his medical
license, a writer who hadn't published a book in 20 years, a husband
who had been divorced from four wives.

Less than 24 hours after he successfully introduced his female
identity to some of his oldest and most respectable Florida friends,
he resurfaced in the nearby community of Key Biscayne.

Perhaps he wanted to celebrate his triumph at a local bar,
a friend says. Maybe he intended to take a walk on the beach.

What is clear is that at about 4 p.m. the next day, Sept. 25,
the burly transsexual was seen parading down a main Key Biscayne
thoroughfare, naked, with a dress and heels in his hand. Taken
into custody by an officer who described him as "very nice"
and perhaps mentally unstable, he was charged with indecent exposure
and resisting arrest without violence.

After a medical exam showed he had undergone a sex change,
he was jailed - on a mere $1,000 bail - at the Miami-Dade Women's
Detention Center.

On Oct. 1, his sixth day in jail, Hemingway, who suffered from
high blood pressure and heart disease, rose early for a court
appearance, began to dress and suddenly collapsed in his underwear
onto the concrete floor.

The third son of the 20th century's most resolutely macho literary
figure had died, at age 69, in a women's jail.

Gregory Hemingway's journey from elephant hunter to bejeweled
exhibitionist, from the boy who appeared to have everything to
the prisoner in cell 3-C2, was long and winding, marked by many
detours and numerous contradictions.

On this much, however, friends and family agree: He suffered
from manic depression, a form of mental illness. Even in a family
tormented by chemical imbalance - Gregory's father, paternal grandfather,
uncle, aunt and niece all committed suicide - the man who sometimes
called himself Gloria was notably tormented.

"He had hundreds of shock treatments, and he kind of got
to like them," says Jeffrey Meyers, who wrote one of several
major biographies of Ernest Hemingway. "It was like an addiction.
Most people are terrified of shock treatments. If you read Sylvia
Plath's 'The Bell Jar,' it's not something you would willingly
do."

There are many who remember Gregory Hemingway as unfailingly
gentle and generous, but when he was in the manic - or euphoric
- stage of his disease he could be reckless, even violent. He
had a string of arrests in Florida and Montana, where he spent
his winters, including one in which he threatened to expose himself
and kicked a police officer in the groin.

Other factors in Hemingway's decline, his associates say, may
have included a chaotic childhood, a complex relationship with
his mother and a sometimes overwhelming desire for acknowledgment
from his famous father.

And then there were the dresses.

At the heart of Hemingway's tangled tale was a lifelong flirtation
with femininity that enraged Ernest, that epitome of swaggering
American machismo, and led to a series of father-son confrontations
that scarred Gregory as a boy and haunted him as an adult.

The battles date back to at least the early 1940s, when, according
to Gregory's friend, the poet Donald Junkins, Ernest walked in
on Gregory - then about 10 - while his athletic young son, the
skeet shooter with the mischievous grin, was trying on his stepmother
Martha Gellhorn's dress and nylons. Ernest "went berserk,"
Junkins says.

Father and son appear to have remained close for several years
after that, with Ernest even tutoring the boy he called Gig for
a career as a writer. But by the time Gregory was 19, he and Ernest
were locked in bloody psychological warfare over the lure of silk
and taffeta.

It was a battle that would span much of the son's life and
continue for decades after the father's death.

***

Ernest Hemingway was a man who got what he wanted: the biggest
fish, the prettiest girl, the Nobel Prize. And in 1931, the man
they called "Papa" wanted a daughter.

The birth of a third son, Gregory Hancock Hemingway, on Nov.
12, was an added complication in an already shaky marriage.

"My father had wanted a daughter badly," Greg wrote
in his 1976 book, "Papa, a Personal Memoir." "So
to my mother, my birth meant that she, or perhaps I, had blown
this last chance to make her lovable egomaniac happy." His
mother, Pauline Pfeiffer, the second of Hemingway's four wives,
left much of Greg's early upbringing to a "'verness"
named Ada, who, according to Greg, tended to respond to even minor
misbehavior by screaming, packing her bags, and fleeing down the
stairs. His father was a warmer figure, and although he was frequently
absent - reporting, writing and romancing his next wife - Greg
adored him.

Strong, stocky and keenly intelligent, the dark-eyed boy, who
fed ducks tenderly and shot them accurately, in many ways resembled
his father, who once said Greg "has the biggest dark side
in the family, except me." Father and son shared a similar
steely determination, and by age 11, Greg was showing signs of
the same athletic gifts.

That was when Ernest entered his son in the Cuban pigeon-shooting
championship. Greg defeated more than 140 contestants, including
some of the best wing shots in the world, to tie for top honors.
There were articles about him in the Havana newspapers. His father
was thrilled. But if there was triumph, there was also tumult.

Ernest ran through four wives by the time Greg was 15. He drank
heavily and allowed his young son to do the same. Greg recalls
in his memoir having his father cheerfully prescribe him a Bloody
Mary - the boy was maybe 12 - as a cure for a hangover.

The conflict over cross-dressing had worsened by 1951, when,
according to the standard account of Hemingway family history,
Greg, then 19, got in trouble over his use of a mind-altering
drug.

THE incident prompted Ernest to lash out viciously at Greg's
mother, Pauline, in a bitter phone call. The story might have
ended there, but unbeknown to anyone, Pauline had a rare tumor
of the adrenal gland that can cause a deadly surge of adrenaline
in times of stress. Within hours of the phone call with Ernest,
she had died of shock on a hospital operating table.

Ernest blamed his son for Pauline's death, and Greg, who was
deeply disturbed by the accusation, never saw his father alive
again.

That basic chronology is not in dispute, but the biographer,
Meyers, now acknowledges that there was an element missing. It
wasn't Greg's drug or alcohol use that caused Ernest to berate
Pauline shortly before she died, he told the Tribune. "I
had to cover that over a little bit in my book, because I was
very close to the family and I really couldn't wound them ..."
Meyers says. "But Ernest knew about Gregory's cross-dressing
way back in '51, and that was the cause of the dispute; not, I
think I called it, drug-taking or drinking." After his mother's
death, Greg, apparently depressed, interrupted his pre-med studies
and retreated to Africa, where he drank too much and shot elephants
- at one point 18 in a single month.

It wasn't until nearly a decade later, in 1960, that he felt
strong enough to resume his medical studies and respond to Ernest's
charges. He wrote his father a bitter letter, detailing the medical
facts of his mother's death and blaming Ernest for the tragedy.

Within months, Ernest showed serious signs of mental illness.
The next year, he would kill himself, and once again Greg would
wrestle with guilt over the death of a parent.

"I never got over a sense of responsibility for my father's
death," he wrote in his memoir, "and the recollection
of it sometimes made me act in strange ways."

***

If Greg was devastated by the death of his father, he also
confessed to a profound sense of relief. As the body was lowered
into the ground, he reflected that never again would he disappoint
the old man.

What followed was perhaps the most productive period of Greg's
life. He graduated from the University of Miami School of Medicine
in 1964, and married what was by now his third wife, Valery Danby-
Smith, the mother of three of his eight children. Living in New
York and Montana, he practiced medicine, the profession of his
paternal grandfather.

"He was a physician at heart," says his eldest daughter,
Lorian, 49, a writer. "The passion was there." In 1976,
he published his book about life with his father. Compassionate
but unflinching, it opened with an admiring introduction by Norman
Mailer and is still highly regarded by Hemingway scholars.

Precisely when Greg's demons caught up with him is unclear,
but by the early 1980s, the storm clouds were gathering. Meyers,
who spent a week with Greg and Valery while researching his book
on Ernest in 1983, recalls that Greg's marriage was breaking up
and he was acting in peculiar, and sometimes reckless, ways.

"He was very good-looking. He was very smart. I mean,
you could have some interesting talks with him. He was also, always,
very crazy," Meyers says.

By the early 1990s, Greg's finances were so precarious - he
was routinely spending every dime of the checks he received monthly
from the family estate - he at one point lived in his beat-up
Volkswagen. Apparently considering a sex change, he had gone so
far as to have a single breast implant, leaving the other side
of his chest flat.

He and Valery had been divorced, and his medical license had
been suspended in both Montana and Florida - the reason is not
known because officials in Montana, where the licensing problems
originated, say they have lost the records.

But when he and Junkins, a Hemingway scholar and retired University
of Massachusetts English professor, began running into each other
socially in Miami in 1991, it wasn't his present problems that
Greg wanted to talk about. It was his past.

He told Junkins, who would later serve as best man at Greg's
fourth wedding, about the fit Ernest threw when he caught Greg
cross-dressing as a boy.

"Gregory was 60 years old, and this is the first thing
he tells me," Junkins says. "He says he never got over
it: the raging wrath of his father." Thirty years after his
death, Ernest Hemingway was back in his son's life.

***

By 1995, the final showdown between father and son was well
under way, with Greg rejecting not only his father's hyper-masculine
code of conduct, but masculinity itself, in an act that some consider
courageous and others depict as the final, desperate act of an
unbalanced mind.

For the most part, Hemingway lived as a man after his sex change.
He had the same deep voice, the same muscular build. Rather than
adding a second breast implant, he had the first removed at some
point in the 1990s.

He stayed with his fourth wife, Ida Mae Galliher, a fine-featured
blonde who drove a Mercedes convertible and was much admired by
Coconut Grove's graying jet-setters. Florida records show the
couple divorced in 1995, after about two years of marriage, but
friends say they continued to live together in Ida's gated coral-rock
cottage.

"He was a very heterosexual guy, I guarantee it,"
Junkins says. "He and Ida weren't putting polish on each
other's nails." Ida, who declined to be interviewed for this
article, told the Miami Herald shortly after Greg's death that
she and Greg remarried in Washington state in 1997.

Hemingway mostly went by the name Greg or Gregory in the Grove,
where he frequented the Taurus Ale House, a neighborhood bar and
restaurant, in men's attire.

"He'd hang out in the afternoon, drink beer with us and
talk," recalls Taurus regular Charley Brown, 62, a writer.
"And he was just one of the guys." Rumors about Greg's
personal life did flourish, and occasionally he would be spotted
cross-dressing. But in resolutely artsy, often bizarre Coconut
Grove, Greg Hemingway wasn't the most unusual guy in the bar.

"Not by a long shot," Brown says.

Hemingway's apparent reluctance to let go of his male identity
could be explained by many factors, among them the potential for
embarrassment. But it does seem a remarkable coincidence that,
in getting a sex change, Greg chose perhaps the one path most
likely to pain and embarrass his father - and then went on living
his life much as before.

It's also interesting to note that when he did assert his femininity,
he sometimes seemed more interested in creating a spectacle than
completing a process of sincere self-transformation.

Perhaps the most dramatic example of that occurred in 1995,
when Hemingway, then 64, boarded a Miami bus, made a series of
sexual advances toward the male driver and threatened to break
his jaw.

When police arrived, Hemingway was standing outside an Amoco
station, dressed in women's clothing and talking incoherently.
Pulling up his skirt, he said to one of the officers, "Let
me show you that I'm a woman." The police officer reminded
him he was in public and told him to put down his skirt. Hemingway
responded by kicking the cop in the groin. It took three police
officers to handcuff Hemingway, who pleaded guilty to a felony
charge of battery on a police officer, but was never convicted.

***

The Miami-Dade Women's Detention Center is a long way from
the Miami of snow-white sailboats and gated Spanish mansions where
Greg Hemingway celebrated the running of the bulls at the annual
Pamplona Party in Coconut Grove.

A battered pay phone stands outside the center, a bland, four-story
building framed by scrub grass, a highway overpass and a series
of rusty pipes enclosed in a chain-link fence.

Inside, the faint smell of disinfectant lingers in a pale green
lobby with peach trim. A row of broad- shouldered, unsmiling women
play volleyball in a narrow courtyard.

Hemingway, who was examined by a corrections medical staff,
was classified as female and assigned here "basically because
of his genital organs," according to Janelle Hall, a spokeswoman
for the Miami-Dade corrections department. "It would have
been an injustice to hold him in a male facility," she says.

Hemingway, who died of heart disease and high blood pressure
on Oct. 1, spent the last days of his life on the third floor,
in a private cell used for high- profile inmates. The room is
10 feet by 10 feet, with a steel cot and two narrow windows.

Staff recall him as "a very big, robust, very learned
sort of person," Hall says. "He did not give us any
problems." At the jail, his death was just another in the
long series of hard-luck tales common to the place. To the outside
world - his obituary, which referred to his sex change and various
psychological problems, ran in publications across the country
- it may have seemed a scandal and sensation.

But in Coconut Grove, where Hemingway was well known and well
liked, it was a tragedy, a tragedy that some say could have been
prevented.

Standing outside the house where Ida Hemingway still lives,
handyman Terry Fox speaks of his friend Greg in the present tense
as he fixes the automatic gate Greg smashed with his car shortly
before his death.

"I don't think they should do that to him, ya know?"
he says of Hemingway's incarceration. "We're real upset about
that. I mean, the average burglar gets out the next day."

Lorian Hemingway goes further, claiming that her father didn't
receive vital medication while in jail.

"I do not know to whom to assign blame," she says,
"But I think his having been incarcerated for five days on
a bail of a mere $1,000 and having his life end because he could
not have the medication he needed is a criminal act, outright."
Ida Hemingway told the Miami Herald that she called the jail repeatedly,
but that she didn't bail Greg out because she thought he needed
help.

Hall declined to comment on whether Hemingway received his
high blood pressure medication in jail, citing inmate confidentiality.
Larry Cameron, director of operations for the Miami-Dade Medical
Examiner Department, declined to comment on medical details, saying
Ida Hemingway had requested that the family's privacy be respected.

Greg Hemingway apparently did not contact his friends, several
of whom said they would have been more than happy to supply the
$100, or 10 percent, required to secure his release on bond.

***

Guests cried openly at Greg's small, private memorial service
in Coconut Grove. Hemingway's children spoke of the good times.

"These kids adored him. It says a lot about Gregory,"
Junkins says. "They know everything. Of course they do. You
know, he was their father."

Exiting the turn-of-the-century Spanish mission church where
the service was held, glancing back at the twin splashes of hot-pink
bougainvillea framing the front door, it must have been easy for
those who attended to think comforting thoughts about God, nature
and the afterlife.

But it's not at all clear that the deceased himself would have
taken refuge in such consolation.

If he had proved one thing during his long and torturous battle
with his father's shadow, it was that he, too, was a Hemingway:
stubborn and self-destructive, but also fierce and uncompromising.

Forty years before, he had considered voicing comforting cliches
at his own father's funeral, he wrote in his memoir.

He had envisioned the old man alive, aware and dreaming, a
spirit united at last with earth and sky.

But, he wrote, such visions seemed small to him, and their
comfort shallow. And his father would have considered such visions
absurd.

"Atoms can't dream, Gig," he could hear his father
say. "No use deluding yourself, old pal."

Chicago Tribune is a Tribune Co. newspaper.

A Family History

IT'S SAFE to say there are few families as fascinating as the
Hemingways. Here is a brief look at some of the family members
and their lives and their problems:

Start, of course, with Ernest. Regarded as one of America's
greatest authors, he won a Pulitzer Prize in 1953 and the Nobel
Prize a year later. His adventures included driving a Red Cross
ambulance during World War I, covering the Spanish Civil War as
a news correspondent and living in Africa, where he went on countless
safaris and survived two plane crashes. All pretty macho stuff.
But he also was the boy whose mother, Grace, dressed him and his
older sister, Marcelline, as twins. Some speculate that was the
root of Ernest's attitude toward women - he long resented Grace
and refused to attend her funeral, married four times and had
countless affairs. He died in 1961, the victim of a self-inflicted
shotgun wound, after years of physical and mental problems. He
was 61.

Clarence Edmonds Hemingway, Ernest's father, took his own life
in 1928. Suffering from diabetes and depression and facing debts,
he shot himself to death with a Civil War pistol. He was 57 years
old.

Grace Hall Hemingway, Ernest's mother, was a former singer
and music teacher. She was extremely protective of her first son.
As he grew older, he rebelled against her nurturing - and later
against her criticism of his work. To friends, he referred to
her as "the bitch." She died in 1951 at 79.

Marcelline Hemingway was Ernest's older sister and the sibling
to whom he was closest. She maintained a famous correspondence
with her brother for many years. Marcelline died in 1963, two
years after Ernest. She was 65.

Ursula Hemingway Jepson, Ernest's younger sister, having survived
three cancer operations, committed suicide with a drug overdose
in 1966. She was 64.

Another sibling, brother Leicester Clarence Hemingway, 67,
shot himself to death in 1982 after a series of health problems.

Carol Hemingway Gardner, Ernest's youngest sister, was estranged
from her brother after he objected to her choice of fiance and
she married the young man anyway. She today is the last surviving
Hemingway sibling.

Madelaine Hemingway Miller, nicknamed "Sunny," typed
portions of her brother's novel "A Farewell to Arms,"
and later played the harp with the Memphis Symphony. She died
in 1995 at the age of 90.

Jack Hemingway, Ernest's oldest son, had a pretty interesting
life in his own right. His godparents were Gertrude Stein and
Alice B. Toklas, whom Ernest had befriended in Paris in the '20s;
his early days were recounted in his father's "A Moveable
Feast"; he was a decorated World War II veteran who spent
six months in a German POW camp; and he wrote several books, including
one about his father, and three on fishing. He died in 2000 of
complications following heart surgery. He was 77.

All of Hemingway's former wives are deceased. Martha Gellhorn,
his third wife, died most recently, in February 1998. Gregory's
mother, Pauline Pfeiffer Hemingway, died in 1951 at age 56 of
an undiagnosed tumor.

Actress/model Margaux Hemingway, 41-year-old daughter of Jack,
died of a drug overdose in 1996. Her younger sister, Mariel, continues
to appear in films and on TV.

Hemingway's sole surviving child is son Patrick, born in 1928.
He continues to promote his father's memory as a member of the
advisory board of the Hemingway Foundation of Oak Park.